Electrochemical Oxidative C-C Bond Cleavage of Ketones for C-N Bond Formation: A Route to Amides

被引:17
|
作者
He, Yonghui [1 ,2 ]
Zeng, Liang [1 ,2 ]
Li, Ming [1 ,2 ]
Gu, Lijun [1 ,2 ,3 ]
Zhang, Shengyong [1 ,2 ]
Li, Ganpeng [1 ,2 ]
机构
[1] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resources, State Ethn Affairs Commiss, Kunming 650500, Yunnan, Peoples R China
[2] Yunnan Minzu Univ, Minist Educ, Kunming 650500, Yunnan, Peoples R China
[3] Guizhou Univ, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期
基金
中国国家自然科学基金;
关键词
METHYL KETONES; METAL-FREE; DIRECT TRANSFORMATION; OXYGENATION; ALDEHYDES;
D O I
10.1021/acs.joc.2c01025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report an efficient electrochemical activation of the C-C bond of aryl ketones for the preparation of amides under catalyst-and external-oxidant-free conditions using aliphatic amines as the N source. Under environmentally benign electrolysis conditions, a series of amides were synthesized in good yield. Our control experiments revealed that electricity plays an important role in this transformation.
引用
收藏
页码:12622 / 12631
页数:10
相关论文
共 50 条
  • [1] Copper-Catalyzed Aerobic Oxidative C-C Bond Cleavage for C-N Bond Formation: From Ketones to Amides
    Tang, Conghui
    Jiao, Ning
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6528 - 6532
  • [2] Nitrogenation of Amides via C-C and C-N Bond Cleavage
    Zhu, Ming -Hui
    Cheng, Zengrui
    Wei, Jialiang
    Tan, Hui
    Jiao, Ning
    CCS CHEMISTRY, 2023, 5 (05): : 1061 - 1068
  • [3] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
    Li, Wenjuan
    Zheng, Xiaojian
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
  • [4] Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
    Wang, Min
    Lu, Jianmin
    Ma, Jiping
    Zhang, Zhe
    Wang, Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14061 - 14065
  • [5] Aerobic Reconstruction of Amines to Amides: A C-N/C-C Bond Cleavage Approach
    Tao, Qinyue
    Zheng, Yanling
    Li, Qiang
    Long, Yang
    Wang, Jing
    Jin, Zewei
    Zhou, Xiangge
    ORGANIC LETTERS, 2024, 26 (51) : 11224 - 11229
  • [6] Oxidative C-S bond cleavage reaction of DMSO for C-N and C-C bond formation: new Mannich-type reaction for β-amino ketones
    Sun, Kai
    Lv, Yunhe
    Zhu, Zhonghong
    Zhang, Liping
    Wu, Hankui
    Liu, Lin
    Jiang, Yongqing
    Xiao, Beibei
    Wang, Xin
    RSC ADVANCES, 2015, 5 (04): : 3094 - 3097
  • [7] Copper-catalyzed and iodide-promoted aerobic C-C bond cleavage/C-N bond formation toward the synthesis of amides
    Wu, Kun
    Huang, Zhiliang
    Ma, Yiyang
    Lei, Aiwen
    RSC ADVANCES, 2016, 6 (29): : 24349 - 24352
  • [8] Electrochemical oxidative C-C bond cleavage of methylenecyclopropanes with alcohols
    Kumar, Rakesh
    Dutt, Shiv
    Banerjee, Prabal
    CHEMICAL COMMUNICATIONS, 2024, 60 (31) : 4246 - 4249
  • [9] TMSCI-Mediated Synthesis of α,β-Unsaturated Amides via C-C Bond Cleavage and C-N Bond Formation of Propargyl Alcohols with Trimethylsilyl Azide
    Song, Xian-Rong
    Song, Bo
    Qiu, Yi-Feng
    Han, Ya-Ping
    Qiu, Zi-Hang
    Hao, Xin-Hua
    Liu, Xue-Yuan
    Liang, Yong-Min
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16): : 7616 - 7625
  • [10] Copper-catalyzed aerobic oxidative C-C bond cleavage of simple ketones for the synthesis of amides
    Yang, Guo-Ping
    Li, Ke
    Liu, Wei
    Zeng, Kai
    Liu, Yu-Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (35) : 6958 - 6964